US8618103B2ActiveUtilityPatentIndex 59
Inhibitors of JAK

Assignee: DE VICENTE FIDALGO JAVIERPriority: Sep 10, 2009Filed: Sep 9, 2010Granted: Dec 31, 2013
Est. expirySep 10, 2029(~3.2 yrs left)· nominal 20-yr term from priority
Inventors:DE VICENTE FIDALGO JAVIER HERMANN JOHANNES CORNELIUS LEMOINE REMY LI HONGJU LOVEY ALLEN JOHN SJOGREN ERIC BRIAN SOTH MICHAEL
A61P 37/02A61P 3/10A61P 35/02A61P 35/00A61P 5/14A61P 37/00A61P 37/08A61P 37/06A61P 29/00A61P 25/00A61P 25/28C07D 487/04A61P 17/06C07D 513/04A61P 17/00A61P 1/04A61P 19/02A61P 11/06C07D 401/14A61K 31/4985
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References
Claims
Abstract

The present invention relates to the use of novel compounds of Formula I, wherein the variables m, n, p, q, Q, r, R, R′, X, X′, Y, Z 1 , Z 2 , and Z 3 are defined as described herein, which inhibit JAK and are useful for the treatment of auto-immune and inflammatory diseases.
Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A compound of Formula I 
       
         
           
           
               
               
           
         
       
       wherein:
 R is lower alkyl, lower haloalkyl, lower alkoxy, hydroxy lower alkyl, hydroxy, or halogen; 
 n is 0 or 1; 
 Z 1  is NH; 
 Z 2  is CH; 
 Z 3  is CR 1 ; 
 R 1  is H, lower alkyl, cycloalkyl, cyano, cyano lower alkyl, or halogen; 
 X is CH, CR′, or N; 
 X′ is CH, CR′, or N; 
 r is 0 or 1; 
 Y is CH, CR′, or N; 
 R′ is R′ a  or R′ b ;
 R′ a  is halogen or cyano; 
 R′ b  is lower alkyl, cycloalkyl, heterocycloalkyl, OR″, SR″, S(═O) 2 R″, or NR″R″, optionally substituted with one or more R′ c ;
 R′ c  is hydroxy, halogen, oxo, cyano, lower alkyl, cycloalkyl, heterocycloalkyl, heteroaryl, carboxy lower alkyl, amino, amino carboxy lower alkyl, lower alkyl amino, lower dialkyl amino, lower haloalkyl, or lower alkoxy; 
 
 
 m is 0 or 1; 
 R″ is H, lower alkyl, hydroxy lower alkyl, heteroaryl, or lower alkoxy; 
 Q is H, S(═O) 2 Q 1 , C(═O)Q 2 , C(═O)OQ 3 , or Q 4 ;
 Q 1  is lower alkyl, cycloalkyl lower alkyl, lower alkyl amino, lower dialkyl amino, or cycloalkyl, optionally substituted with one or more Q 1′ ;
 each Q 1′  is independently halogen, lower alkyl, cyano, or lower alkoxy; 
 
 Q 2  is lower alkyl, cycloalkyl lower alkyl, or cycloalkyl, optionally substituted with one or more Q 2′ ;
 each Q 2′  is independently halogen, lower alkyl, cyano, or lower alkoxy; 
 
 Q 3  is lower alkyl, cycloalkyl lower alkyl, or cycloalkyl, optionally substituted with one or more Q 3′ ;
 each Q 3′  is independently halogen, lower alkyl, or lower alkoxy; 
 
 Q 4  is lower alkyl, cycloalkyl lower alkyl, heterocycloalkyl, or cycloalkyl, optionally substituted with one or more Q 4′ ;
 each Q 4′  is independently halogen, cyano, cyano lower alkyl, lower alkyl, or lower alkoxy; 
 
 
 p is 0, 1, or 2; 
 q is 1 or 2; 
 each   represents a single bond or a double bond; and 
 with the proviso that the bonds between Z 1  and Z 2  and Z 2  and Z 3  are not both double bonds and are not both single bonds; 
 
       or a pharmaceutically acceptable salt thereof. 
     
     
       2. The compound of  claim 1 , having the Formula II 
       
         
           
           
               
               
           
         
       
       wherein:
 R is lower alkyl; 
 n is 0 or 1; 
 Z 3  is CR 1 ; 
 R 1  is H, lower alkyl, or halogen; 
 X is CH, CR′, or N; 
 Y is CH, CR′, or N; 
 R′ is R′ a  or R′ b ;
 R′ a  is halogen or cyano; 
 R′ b  is lower alkyl, cycloalkyl, heterocycloalkyl, OR″, SR″, S(═O) 2 R″, or NR″R″, optionally substituted with one or more R′ c ;
 R′ c  is hydroxy, halogen, oxo, cyano, lower alkyl, cycloalkyl, heterocycloalkyl, heteroaryl, carboxy lower alkyl, amino, amino carboxy lower alkyl, lower alkyl amino, lower dialkyl amino, lower haloalkyl, or lower alkoxy; 
 
 
 m is 0 or 1;
 R″ is H, lower alkyl, hydroxy lower alkyl, heteroaryl, or lower alkoxy; 
 
 Q is H, S(═O) 2 Q 1 , C(═O)Q 2 , C(═O)OQ 3 , or Q 4 ;
 Q is H, S(═O) 2 Q 1 , C(═O)Q 2 , C(═O)OQ 3 , or Q 4 ; 
 Q 1  is lower alkyl, cycloalkyl lower alkyl, lower alkyl amino, lower dialkyl amino, or cycloalkyl, optionally substituted with one or more Q 1′ ;
 each Q 1′  is independently halogen, lower alkyl, cyano, or lower alkoxy; 
 
 Q 2  is lower alkyl, cycloalkyl lower alkyl, or cycloalkyl, optionally substituted with one or more Q 2′ ;
 each Q 2′  is independently halogen, lower alkyl, cyano, or lower alkoxy; 
 
 Q 3  is lower alkyl, cycloalkyl lower alkyl, or cycloalkyl, optionally substituted with one or more Q 3′ ;
 each Q 3′  is independently halogen, lower alkyl, or lower alkoxy; 
 
 Q 4  is lower alkyl, cycloalkyl lower alkyl, heterocycloalkyl, or cycloalkyl, optionally substituted with one or more Q 4′ ;
 each Q 4′  is independently halogen, cyano, cyano lower alkyl, lower alkyl, or lower alkoxy; 
 
 
 p is 0, 1, or 2; 
 q is 1 or 2; and 
 
       or a pharmaceutically acceptable salt thereof. 
     
     
       3. The compound of  claim 2 , wherein Z 3  is CH. 
     
     
       4. The compound of  claim 3 , wherein X is CH and Y is CH. 
     
     
       5. The compound of  claim 4 , wherein m is 0 and n is 0. 
     
     
       6. The compound of  claim 5 , wherein p is 1 and q is 1. 
     
     
       7. The compound of  claim 5 , wherein p is 0 and q is 1. 
     
     
       8. The compound of  claim 6 , wherein Q is S(═O) 2 Q′. 
     
     
       9. The compound of  claim 8 , wherein Q 1  is lower alkyl. 
     
     
       10. The compound of  claim 8 , wherein Q 1  is cycloalkyl lower alkyl. 
     
     
       11. The compound of  claim 7 , wherein Q is S(═O) 2 Q 1 . 
     
     
       12. The compound of  claim 11 , wherein Q 1  is lower alkyl. 
     
     
       13. The compound of  claim 6 , wherein Q is C(═O)Q 2  and Q 2  is lower alkyl. 
     
     
       14. The compound of  claim 7 , wherein Q is C(═O)Q 2  and Q 2  is lower alkyl. 
     
     
       15. The compound of  claim 6 , wherein Q is C(═O)OQ 3  and Q 3  is lower alkyl. 
     
     
       16. The compound of  claim 7 , wherein Q is C(═O)OQ 3  and Q 3  is lower alkyl. 
     
     
       17. The compound of  claim 4 , wherein p is 1, q is l, m is 1, n is 0, and R′ is lower alkyl. 
     
     
       18. The compound of  claim 4 , wherein p is 1, q is l, m is 0, n is 1, and R″ is lower alkyl. 
     
     
       19. The compound of  claim 17 , wherein Q is S(═O) 2 Q′. 
     
     
       20. The compound of  claim 19 , wherein Q 1  is lower alkyl. 
     
     
       21. The compound of  claim 19 , wherein Q 1  is cycloalkyl lower alkyl. 
     
     
       22. The compound of  claim 18 , wherein Q is S(═O) 2 Q′. 
     
     
       23. The compound of  claim 22 , wherein Q 1  is lower alkyl. 
     
     
       24. The compound of  claim 22 , wherein Q 1  is cycloalkyl lower alkyl. 
     
     
       25. A compound selected from the group consisting of:
 ((S)-1-Methanesulfonyl-piperidin-3-yl)-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 ((R)-1-Methanesulfonyl-piperidin-3-yl)-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 1-{(R)-3-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-pyrrolidin-1-yl}-ethanone; 
 (R)-3-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-pyrrolidine-1-carboxylic acid methyl ester; 
 ((R)-1-Methanesulfonyl-pyrrolidin-3-yl)-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 1-{(R)-3-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-piperidin-1-yl}-ethanone; 
 4-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-piperidine-1-carboxylic acid methyl ester; 
 1-{4-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-piperidin-1-yl}-ethanone; 
 1-{(S)-3-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-pyrrolidin-1-yl}-ethanone; 
 (S)-3-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-pyrrolidine-1-carboxylic acid methyl ester; 
 ((S)-1-Methanesulfonyl-pyrrolidin-3-yl)-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 1-{3-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-azepan-1-yl}-ethanone; 
 3-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-azepane-1-carboxylic acid methyl ester; 
 (1-Methanesulfonyl-azepan-3-yl)-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 [(R)-1-(Propane-2-sulfonyl)-piperidin-3-yl]-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 ((R)-1-Ethanesulfonyl-pyrrolidin-3-yl)-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 [(R)-1-(Propane-1-sulfonyl)-pyrrolidin-3-yl]-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 [(R)-1-(Propane-2-sulfonyl)-pyrrolidin-3-yl]-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 [(R)-1-(2-Methyl-propane-1-sulfonyl)-pyrrolidin-3-yl]-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 1-{(R)-3-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-pyrrolidin-1-yl}-propan-1-one; 
 1-{(R)-3-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-pyrrolidin-1-yl}-butan-1-one; 
 2-Methyl-1-{(R)-3-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-pyrrolidin-1-yl}-propan-1-one; 
 3-Methyl-1-{(R)-3-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-pyrrolidin-1-yl}-butan-1-one; 
 ((3S,5S)-1-Methanesulfonyl-5-methyl-piperidin-3-yl)-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 [(3S,5S)-5-Methyl-1-(propane-1-sulfonyl)-piperidin-3-yl]-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 [(3S,5S)-5-Methyl-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 [(R)-1-(3-Methyl-butane-1-sulfonyl)-pyrrolidin-3-yl]-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 [(3S,5S)-5-Methyl-1-(propane-2-sulfonyl)-piperidin-3-yl]-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 [(S)-1-(2-Methyl-propane-1-sulfonyl)-piperidin-3-yl]-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 1-{3-[6-Methyl-3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-piperidin-1-yl}-ethanone; 
 (1-Methanesulfonyl-piperidin-3-yl)-[6-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 [(S)-1-(2,2-Dimethyl-propane-1-sulfonyl)-piperidin-3-yl]-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 [3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-[(S)-1-(2,2,2-trifluoro-ethyl)-piperidin-3-yl]-amine; 
 (1-Ethanesulfonyl-piperidin-3-yl)-[6-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 (1-Cyclopropylmethanesulfonyl-piperidin-3-yl)-[6-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 [1-(2,2-Dimethyl-propane-1-sulfonyl)-piperidin-3-yl]-[6-methyl-3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 (1-Methanesulfonyl-azepan-4-yl)-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 ((S)-1-Cyclopropylmethanesulfonyl-piperidin-3-yl)-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 1-{3-[3-(7-Chloro-5H-pyrrolo[2,3-b]pyrazin-2-yl)-6-methyl-pyridin-2-ylamino]-piperidin-1-yl}-ethanone; 
 [3-(7-Chloro-5H-pyrrolo[2,3-b]pyrazin-2-yl)-6-methyl-pyridin-2-yl]-(1-cyclopropylmethanesulfonyl-piperidin-3-yl)-amine; 
 ((S)-1-Methanesulfonyl-piperidin-3-yl)-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrazin-2-yl]-amine; 
 {(S)-3-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-piperidine-1-sulfonyl}-acetonitrile; 
 [(S)-1-(2-Methyl-propane-1-sulfonyl)-piperidin-3-yl]-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrazin-2-yl]-amine; 
 2-[2-((S)-1-Methanesulfonyl-piperidin-3-ylamino)-pyridin-3-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carbonitrile; 
 ((S)-1-Methanesulfonyl-piperidin-3-yl)-[3-(7-methyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 [3-(7-Cyclopropyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-((S)-1-methanesulfonyl-piperidin-3-yl)-amine; 
 [3-(7-Chloro-5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-((S)-1-methanesulfonyl-piperidin-3-yl)-amine; 
 (3R,4R)-1-(2-Methyl-propane-1-sulfonyl)-3-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-piperidin-4-ol; 
 (3R,4R)-1-Methanesulfonyl-3-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-piperidin-4-01; 
 (S)-3-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-piperidine-1-sulfonic acid dimethylamide; 
 (S)-3-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-piperidine-1-sulfonic acid tert-butylamide; 
 ((S)-1-Methanesulfonyl-piperidin-3-yl)-[5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine; 
 [(S)-1-(2-Methyl-propane-1-sulfonyl)-piperidin-3-yl]-[5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine; 
 N4-[(S)-1-(2-Methyl-propane-1-sulfonyl)-piperidin-3-yl]-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidine-2,4-diamine; 
 N2,N2-Dimethyl-N-4-[(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidine-2,4-diamine; 
 [2-Methanesulfonyl-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-[(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-amine; 
 [(S)-1-(2-Methyl-propane-1-sulfonyl)-piperidin-3-yl]-[2-methylsulfanyl-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine; 
 [(S)-1-(2-Methyl-propane-1-sulfonyl)-piperidin-3-yl]-[2-morpholin-4-yl-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine; 
 ((S)-1-Methanesulfonyl-piperidin-3-yl)-[2-methylsulfanyl-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine; 
 N4-((S)-1-Methanesulfonyl-piperidin-3-yl)-N2,N2-dimethyl-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidine-2,4-diamine; 
 N4-((S)-1-Methanesulfonyl-piperidin-3-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidine-2,4-diamine; 
 2-[2-Dimethylamino-4-((S)-1-methanesulfonyl-piperidin-3-ylamino)-pyrimidin-5-yl]-5H-pyrrolo[2,3-b]pyrazine-7-carbonitrile; 
 [(S)-1-(3,3-Dimethyl-butane-1-sulfonyl)-piperidin-3-yl]-[2-methylsulfanyl-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine; 
 ((S)-1-Methanesulfonyl-piperidin-3-yl)-[2-methoxy-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine; 
 [2-Chloro-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-((S)-1-methanesulfonyl-piperidin-3-yl)-amine; 
 ((S)-1-Methanesulfonyl-piperidin-3-yl)-[2-(4-methyl-piperazin-1-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine; 
 4-((S)-1-Methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-2-ol; 
 [2-Ethoxy-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-((S)-1-methanesulfonyl-piperidin-3-yl)-amine; 
 2-[4-((S)-1-Methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-2-ylamino]-ethanol; 
 N4-((S)-1-Methanesulfonyl-piperidin-3-yl)-N2-(2-methoxy-ethyl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidine-2,4-diamine; 
 ((S)-1-Methanesulfonyl-piperidin-3-yl)-[2-morpholin-4-yl-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine; 
 3-{(S)-3-[2-Methylsulfanyl-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-ylamino]-piperidin-1-yl}-3-oxo-propionitrile; 
 1-[4-((S)-1-Methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-2-ylamino]-2-methyl-propan-2-ol; 
 [2-(1,1-Dioxo-1λ6-thiomorpholin-4-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-((S)-1-methanesulfonyl-piperidin-3-yl)-amine; 
 ((S)-1-Methanesulfonyl-piperidin-3-yl)-[2-(4-methoxy-piperidin-1-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine; 
 N2-(2-Amino-ethyl)-N4-((S)-1-methanesulfonyl-piperidin-3-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidine-2,4-diamine; 
 2-{1-[4-((S)-1-Methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-2-yl]-piperidin-4-yl}-acetamide; 
 (S)-2-[4-((S)-1-Methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-2-ylamino]-butan-1-ol; 
 (R)-2-[4-((S)-1-Methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-2-ylamino]-butan-1-ol; 
 N4-((S)-1-Methanesulfonyl-piperidin-3-yl)-N2-(1-methyl-piperidin-4-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidine-2,4-diamine; 
 [(S)-1-(3,3-Dimethyl-butane-1-sulfonyl)-piperidin-3-yl]-[2-(4-methyl-piperazin-1-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine; 
 [2-(4-Dimethylamino-piperidin-1-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-((S)-1-methanesulfonyl-piperidin-3-yl)-amine; 
 4-((S)-1-Methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidine-2-carbonitrile; 
 (S)-1-[4-((S)-1-Methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-2-yl]-pyrrolidin-3-ol; 
 (R)-1-[4-((S)-1-Methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-2-yl]-pyrrolidin-3-ol; 
 1-[4-((S)-1-Methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-2-yl]-azetidine-3-carbonitrile; 
 4-[4-((S)-1-Methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-2-ylamino]-cyclohexanecarbonitrile; 
 ((S)-1-Methanesulfonyl-piperidin-3-yl)-[2-(4-pyridin-2-yl-piperazin-1-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine; 
 {1-[4-((S)-1-Methanesulfonyl-piperidin-3-ylamino)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-2-yl]-piperidin-4-yl}-acetic acid; 
 N4-((S)-1-Methanesulfonyl-piperidin-3-yl)-N2-pyridin-4-yl-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidine-2,4-diamine; 
 N2-(2-Dimethylamino-ethyl)-N4-((S)-1-methanesulfonyl-piperidin-3-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidine-2,4-diamine; 
 [2-(4-Ethyl-piperazin-1-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-((S)-1-methanesulfonyl-piperidin-3-yl)-amine; 
 [2-((R)-3-Dimethylamino-pyrrolidin-1-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-((S)-1-methanesulfonyl-piperidin-3-yl)-amine; 
 [2-(4-Methyl-piperazin-1-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-[(S)-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-amine; 
 [(3S,5S)-5-Methyl-1-(2-methyl-propane-1-sulfonyl)-piperidin-3-yl]-[2-(4-methyl-piperazin-1-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine; 
 {(3S,5S)-3-Methyl-5-[2-(4-methyl-piperazin-1-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-ylamino]-piperidine-1-sulfonyl}-acetonitrile; 
 ((3S,5S)-1-Methanesulfonyl-5-methyl-piperidin-3-yl)-[2-(4-methyl-piperazin-1-yl)-5-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyrimidin-4-yl]-amine; 
 ((3S,5S)-1-Methanesulfonyl-5-trifluoromethyl-piperidin-3-yl)-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 [(3S,5S)-1-(2-Methyl-propane-1-sulfonyl)-5-trifluoromethyl-piperidin-3-yl]-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-yl]-amine; 
 (3-{(S)-3-[3-(5H-Pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-piperidin-1-yl}-oxetan-3-yl)-acetonitrile; 
 (3-{(3S,5S)-3-Methyl-5-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-piperidin-1-yl}-oxetan-3-yl)-acetonitrile; 
 {(3S,5S)-3-Methyl-5-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-piperidine-1-sulfonyl}-acetonitrile; and 
 4,4,4-Trifluoro-3-{(S)-3-[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)-pyridin-2-ylamino]-piperidin-1-yl}-butyronitrile. 
 
     
     
       26. A pharmaceutical composition comprising the compound of  claim 1 , admixed with at least one pharmaceutically acceptable carrier, excipient or diluent. 
     
     
       27. The pharmaceutical composition of  claim 26 , further comprising an additional therapeutic agent selected from a chemotherapeutic or anti-proliferative agent, an anti-inflammatory agent, an immunomodulatory or immunosuppressive agent, a neurotrophic factor, an agent for treating cardiovascular disease, an agent for treating diabetes, and an agent for treating immunodeficiency disorders.
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